Etymology

rake-stepping

Today it means: The act of repeatedly making damaging and avoidable mistakes. Full definition →

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The story

Popularized by a gag in the 1993 episode "Cape Feare" of The Simpsons, in which Sideshow Bob, already injured, accidentally steps on several rakes, causing the handles to hit him in the face.

Etymology from Wiktionary, CC BY-SA 4.0.